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SML3414

Sigma-Aldrich

GW627368X

≥98% (HPLC)

Synonym(s):

2-(4-(4,9-Diethoxy-1-oxo-1H-benzo[f]isoindol-2(3H)-yl)phenyl)-N-(phenylsulfonyl)acetamide, 4-(4,9-Diethoxy-1,3-dihydro-1-oxo-2H-benz[f]isoindol-2-yl)-N-(phenylsulfonyl)benzeneacetamide, GW 627368, GW 627368X, GW-627368, GW-627368X, GW627368

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About This Item

Empirical Formula (Hill Notation):
C30H28N2O6S
CAS Number:
439288-66-1
Molecular Weight:
544.62
MDL number:
MFCD12912327
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

SMILES string

O=C(CC1=CC=C(C=C1)N(C2=O)CC3=C2C(OCC)=C4C=CC=CC4=C3OCC)NS(=O)(C5=CC=CC=C5)=O

InChI

1S/C30H28N2O6S/c1-3-37-28-23-12-8-9-13-24(23)29(38-4-2)27-25(28)19-32(30(27)34)21-16-14-20(15-17-21)18-26(33)31-39(35,36)22-10-6-5-7-11-22/h5-17H,3-4,18-19H2,1-2H3,(H,31,33)

InChI key

XREWXJVMYAXCJV-UHFFFAOYSA-N

Biochem/physiol Actions

GW627368X is a potent and selective prostaglandin E2 receptor EP4 antagonist with additional affinity for thromboxane A2 receptor (pKi = 7.0/EP4, 6.8/TP, <5.3/DP, EP1, EP2, EP3, FP & IP) that effectively reduces basal (non-detectable at 0.1 nM with COX inhibition or pIC50 = 6.3 without) and PGE2-stimulated cAMP (pKb = 7.9) in human EP4-expressing HEK293 cells. GW627368X inhibits EP4-, but not EP2-, induced tissue relaxation (pKb = 9.2; precontracted piglet & rabbit saphenous vein), but not TP agonist U46619-elevated tissue tone (pKb <5) ex vivo, and blocks PGE2-enhanced HBV virus replication in mice in vivo (1 mg/kg/day i.p.) by preventing CD8 + T-cell impairment by PGE2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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J F Hiken et al.
Oncogene, 36(16), 2319-2327 (2016-11-22)
Approximately 75% of breast cancers express estrogen receptor α (ERα) and depend on estrogen signals for continued growth. Aromatase inhibitors (AIs) prevent estrogen production and inhibit ER signaling, resulting in decreased cancer recurrence and mortality. Advanced tumors treated with AIs
Tomomi Ohmura et al.
Molecular biology of the cell, 28(12), 1622-1635 (2017-04-22)
The role of prostaglandin A2 (PGA2) in modulation of vascular endothelial function is unknown. We investigated effects of PGA2 on pulmonary endothelial cell (EC) permeability and inflammatory activation and identified a receptor mediating these effects. PGA2 enhanced the EC barrier
Jamie M Golden et al.
American journal of physiology. Gastrointestinal and liver physiology, 315(2), G259-G271 (2018-04-20)
The intestinal barrier is often disrupted in disease states, and intestinal barrier failure leads to sepsis. Ursodeoxycholic acid (UDCA) is a bile acid that may protect the intestinal barrier. We hypothesized that UDCA would protect the intestinal epithelium in injury

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